Jamestown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Teresa Durrant Pierce

Top hotels in Jamestown

Lake Cumberland State Resort Park
Lake Cumberland State Resort Park
3 out of 5
5465 State Park Rd, Jamestown, KY
8.6/10 Excellent! (459 reviews)
"Lovely"

Reviewed on 19 May 2025

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Lake Cumberland State Resort Park
Timber Pointe Resort
Timber Pointe Resort
2 out of 5
2671 Kentucky 92, Jamestown, KY
The price is 3.661.129 ₫ per night from 13 Jul to 14 Jul
3.661.129 ₫
4.035.853 ₫ total
13 Jul - 14 Jul
includes taxes & fees
10/10 Exceptional! (5 reviews)
"A very pleasant stay"

Reviewed on 29 Mar 2025

Timber Pointe Resort
Days Inn by Wyndham Columbia Kentucky
Days Inn by Wyndham Columbia Kentucky
2.5 out of 5
710 Bomar Hts, Columbia, KY
Fully refundableReserve now, pay when you stay
The price is 2.195.894 ₫ per night from 9 Jul to 10 Jul
2.195.894 ₫
2.490.583 ₫ total
9 Jul - 10 Jul
includes taxes & fees
8.2/10 Very Good! (470 reviews)
"An excellent value for the price *****"

Reviewed on 20 Jun 2025

Days Inn by Wyndham Columbia Kentucky
See all 554 properties in Jamestown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Jamestown holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. But how much your holiday to Jamestown costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Jamestown?
December, January and February are the best times to look for cheap Jamestown holiday packages. Opting to travel in quieter months means you can usually find better prices on hotels and flights.
How many days is enough for Jamestown?
The ideal duration of your Jamestown holiday depends on what you'd like to do. Typically, a handful of days to a week will give you time to go to all the leading attractions and explore some hidden spots along the way.
How to find the best Jamestown package deals?
Use Expedia's filters to help you find some great Jamestown package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Jamestown package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book a Jamestown holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still have the freedom to create a tailored Jamestown holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Jamestown?
Enjoy incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Jamestown escape.
How to plan a trip to Jamestown?

  1. Choose when to go: Check your schedule and pack your bags. Your preferred season and the activities on offer will also help you decide when to holiday in Jamestown.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and dining out to airfares and activities. Your accommodation will probably be the largest expense during your trip to Jamestown.
  3. Work out your trip length: Consider how much time you want to spend exploring Jamestown. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  4. Combine your accommodation and airfare: Once you've settled on your trip dates and duration, book the right Jamestown holiday package for you.

Popular places to visit

Lake Cumberland State Resort Park

Lake Cumberland State Resort Park

Explore the great outdoors at Lake Cumberland State Resort Park, a lovely green space in Jamestown. Stroll along the lakeside or seek out the fishing spots.

Lake Cumberland State Resort Park